luxury houses with pool for sale Pound Ridge, United States

Enter a world of opulent privacy on nearly twenty-five acres of pristine countryside, boasting five acres of serene lakes, an elegant stone bridge, and expansive manicured lawns that cradle an entire valley just 45 miles from NYC. Discover a lavish retreat comprising of four distinct residences: a magnificent five-bedroom, four-bathroom main estate, a charming two-bedroom, two-bathroom guest cottage, a sophisticated two-bedroom, one-bathroom carriage house complete with a heated three-car garage, and a stylish one-bedroom, one-bathroom log cabin pool house overlooking a 20x50 heated saltwater pool. Additionally, luxuriate in a cozy writers cabin, with a majestic fireplace. The compound also has a versatile storage barn with separate private driveway access and a dog kennel. The property is artfully situated amidst majestic oak trees and vibrant flowering shrubs, adorned with professionally landscaped stone terraces, walls, and scenic viewpoints, featuring multiple rose and mixed flower gardens, an organic vegetable garden, and a host of other exquisite amenities. Stroll through this picturesque sanctuary of unmatched serenity - a truly enchanting haven of natural beauty and modern comforts.

Presenting the historic Landis Gores House, an architectural masterpiece epitomizing post-WWII Modernism. Designed in 1946 by Harvard Five architect Landis Gores for his own family, it stands proudly as one of New Canaan's first Modern homes. Gores was at that time working in association with Philip Johnson. He set his own home on a narrow granite ridge astride a majestic 4-acre wooded lot; the residence brilliantly leavens the glass-walled austerity of the International Style with the natural warmth of Wrightian organic architecture.The 130-foot long, single-story form is defined by sweeping horizontal planes, full-height plate glass walls, grey-stained cypress siding, and by natural stone fireplaces, walls and terracing. Its informal, open plan is divided into three distinct pavilions, anchored by the dramatic central living and dining area featuring a raised roof and tall ceilings. Original exterior lighting design by Richard Kelly enhances the seamless integration between the avant-garde interior and its environment. An expansive rear terrace, added by Gores himself in the 1980s, features circular seating areas and an elegant oval swimming pool.Listed on the National Register of Historic Places in 2002 and held by the Gores family since its inception. The Gores family granted a perpetual preservation easement to the National Trust for Historic Preservation. This iconic property offers a once-in-a-lifetime opportunity to own a foundational piece of architectural history

Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated gunite pool and pool house, added in 1991, offer a true retreat setting, complete with a party room, kitchen, bedroom, bath, and sauna for a resort like experience. A rare opportunity to own a private New Canaan estate with exceptional grounds, flexibility of living, and proximity to town.

'La Gentilhommière' is a unique property in North Stamford, inspired by Château de Givenchy-le-Noble in France. Built 20 years ago, this property exudes an authentic French charm with imported materials gracing its construction. From the stately Pierre de Bourgogne limestone that adorns its exterior to the exquisite 18th-century French elements found within, every detail evokes a sense of timeless elegance. Inside, you'll discover the beauty of Versailles wood parquet flooring and the comfort of double-paned insulated windows, each adorned with brass European-style handles that enhance the estate's allure. The heart of the home showcases a Smallbone kitchen, complete with a La Cornue Château range, while radiant-heated floors and numerous other exceptional features elevate this property to a class of its own. Bordering the Helene Altschul Land Trust, ensuring no adjacent construction, the privacy in this estate is second to none. The property includes 2 newly built guest houses, one pool house featuring a kitchen with a private bathroom, and a studio house with an inspiring view to stimulate the mind. The newly built 12 meter pool is surrounded by amazing landscapes, as the large schist boulders are reminiscent of Central Park. Combining historical aspects that cannot be duplicated, in addition to the modernized renovations, this property will appeal to anybody with its unprecedented versatility. Conveniently close to the Merritt Parkway and Manhattan, it offers a rare opportunity for discerning buyers looking for quick access to the city.

Cosseted within the gates of the exclusive Conyers Farm association with 24hr security, this baronial French Normandy chateau is poised on more than thirteen park-like acres. Hospitality sets the tone from the entrance through the grand foyer to the dual living rooms, an impressive formal dining room for large-scale entertaining and a warmly paneled library. The heart of the home is the luxurious kitchen with butler's pantry, breakfast room and adjoining family room with fireplace. French doors open to the immense terrace, perfect for outdoor dining. A true sanctuary, the primary suite features two bathrooms, two sizable walk-in closets, a dressing room and a romantic sitting room with balcony overlooking the naturally secluded, private backyard. Six additional bedrooms offer abundant space for guests or family. Creating captivating vignettes of multifunctional living, the lower level features a home theater, sitting room with fireplace, full bar with kitchenette, gym, indoor resistance pool and a hot tub. Outside the terrace overlooks beautiful, level lawns and a pool with spa. Peace of mind is the directive for this characterful estate, with its reassuring security in a guard-gated enclave and its luxury leisure amenities.

Hidden away at the end of a coveted West Side cul-de-sac, 48 Driftway Lane is a private estate tucked among the winding back roads of New Canaan. Perched atop 1.62 beautifully landscaped acres and surrounded by nature, the setting offers a rare sense of peace and privacy, yet remains just minutes from downtown New Canaan and approximately one hour from New York City. Newly constructed from the ground up in 2017 and offering over 10,000 square feet of thoughtfully curated living space, the home unfolds through a series of light-filled rooms where architectural detail, craftsmanship, and connection take center stage. A grand central foyer showcases a statement staircase framed by glass railings, creating a stunning focal point from the moment you enter. At the heart of the home, a sunlit gathering space serves as the natural connection point between the designer kitchen, soaring two-story family room, and outdoor living spaces beyond. Anchored by a stunning 10-foot quartzite waterfall island and matching custom quartzite hood, the kitchen balances beauty and function with Thermador appliances, Sub-Zero refrigeration and wine storage, custom cabinetry, and a walk-in pantry. The dramatic family room draws the eye upward with soaring ceilings, extensive architectural detailing, automated Lutron shades, and walls of windows that flood the space with natural light.

Iconic stone estate on nearly five level acres with sprawling lawns, three bedroom guest cottage, two bedroom caretaker's barn and 50' pool. This home offers six+ bedrooms, nine baths and room for everyone. Entertain on a grand scale with your very own ballroom with 20'ceilings, dining room that seats 22 and beautiful formal rooms. Enjoy smaller family gatherings in the expansive kitchen, family and garden rooms, parlors or library. Twelve foot ceilings, gorgeous herringbone floors, incredible moldings and original details throughout the house. This estate has many updates including a new, super cost efficient Geothermal HVAC system, whole house generator, well pump, water filtration system, 7 new baths and much more. This remarkable residence provides a sense of seclusion while still being conveniently located near all amenities and only 50 minutes to Manhattan.

Prestigious Hoyt Farm Tudor: An Elegant Two-Acre Oasis Near the Village. Nestled on two beautifully landscaped, ultra-private acres in the highly coveted Hoyt Farm neighborhood, this exceptional Tudor offers over 7,400 square feet of sophisticated luxury and warmth. A grand, two-story foyer welcomes you into a seamless, light-filled layout featuring a formal living room with dramatic vaulted ceilings, a handsome wood-paneled library, and an open chef's kitchen that flows effortlessly into a spacious family room with a fireplace. The primary suite is a true sanctuary, boasting its own cozy fireplace, a private balcony overlooking the grounds, a generous dressing room, and a sun-drenched, spa-like bath. Four additional bedrooms and four-and-a-half baths ensure plenty of space and comfort for everyone. Outside, your personal resort awaits: host gatherings on the tranquil brick terrace by the outdoor fireplace, swim in the stunning heated pool, or simply enjoy the park-like property framed by mature specimen trees. Complete with a three-car garage, this magnificent estate offers unparalleled privacy and convenience, located just minutes from the train, vibrant village life, and top-rated New Canaan schools.

Overlooking Wilshire Pond, 35 Wilshire Road is a rare modern backcountry compound set on 5.29 private acres with a true resort-like feel. Designed by noted architect Gerald Schiff, the home offers approx. 7,884 sq ft, 8 total beds & baths, bold entertaining spaces, and dramatic architectural details throughout. Amenities include a natural pool with waterfall and 15+ ft deep diving well, stone pool house with guest suite, tennis court with stadium lighting, expansive sports lawn, renovated gym with floor-to-ceiling windows, 3-car garage and generator. Substantially improved by the current owners, with reimagined landscaping, enhanced living spaces & upgraded systems, this is a one-of-a-kind Greenwich retreat is designed for privacy, recreation and effortless entertaining.

A rare offering in back-country Greenwich, this timeless estate is set on 3.58 exquisitely landscaped and gated acres, masterfully blending classic architecture with contemporary luxury. Designed for both grand-scale entertaining and intimate everyday living, the residence offers a sun-filled interior with soaring ceilings, custom millwork, and modern, bespoke finishes throughout. The grand foyer of this center hall colonial sets the tone for elegant, refined living. The gourmet marble kitchen opens to a multi-exposure family room with sweeping views of the manicured yard, pool, and fully equipped outdoor kitchen. The grounds are equally captivating, with a tranquil koi pond enhancing the natural beauty of the landscape. The luxurious primary suite with sitting area, spa-inspired bath, and three walk-in closets is among five second-level bedroom suites, each offering exceptional privacy and comfort. A versatile second-level suite with private entrance currently functions as a private gym but can effortlessly serve as an au pair suite or guest quarters. The thoughtfully executed lower level is fit with a theater, bar, wine cellar, and recreation spaces. The pool house extends the living experience with two additional bedrooms and two full baths-set amidst expansive patios and a lush, tree-lined lawn. Located just minutes from town, schools, and 45 minutes to Manhattan, this meticulously designed compound offers a rare blend of serenity, sophistication, and convenience.

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence. Merrit to Round Hill Road

Set on over two acres of exquisitely manicured grounds, this exceptional six-bedroom Georgian estate offers approximately 8,500 square feet of elegant living space, including the finished lower level. Beautifully proportioned interiors feature refined formal rooms, a chef's kitchen with premium appliances and marble island, an inviting family room, library, and a luxurious primary suite with sitting room and spa-inspired bath. Designed for effortless indoor-outdoor living, the resort-style grounds showcase a spectacular pool and spa, expansive terraces, outdoor kitchen with pizza oven and grills, fire pit, greenhouse, and organic gardens. Complete with a heated three-car garage and approved seven-bedroom replacement area, this is a rare Greenwich offering.

This stunning Round Hill estate in Greenwich, Connecticut is set in a private, knoll-top setting that ensures tranquility and picturesque views. The exquisite property spans four glorious acres and features six spacious bedrooms and four and a half baths, providing ample room for family and guests. Enjoy beautiful east and west exposures that fill the home with natural light. The layout is perfect for entertaining, with large living areas flowing seamlessly into the outdoors. French doors open to a lovely level yard, complete with an inviting pool and historic barn, making it an ideal space for gatherings and leisure. Move in as-is or take advantage of the abundant potential for expansion. Don't miss the chance to make this exceptional estate your own!

Set majestically on nearly three gated acres in Armonk’s coveted Wrights Mill Estates, this extraordinary hand-cut stone manor with over 12,000 sq ft of classic architecture, artisan craftsmanship, and resort-caliber living. A breathtaking foyer leads to the two-story great room with an impressive window wall and fireplace. A richly paneled study and sunlit conservatory offer space for dual home offices. A family room, dining room, chef’s kitchen with pantry and breakfast room, complete the main level. The upper level offers a grand primary suite, a luxurious retreat featuring a fireplace, dual spa baths, separate dressing rooms, and a third-floor private wellness space with sauna. Additionally, upstairs, four ensuite bedrooms, laundry room and den are joined by a dramatic enclosed bridge leading to a private guest wing. The lower level rivals a private club with lounge, wet bar, wine cellar, theater, gym, hot yoga studio, bedroom, bath and second laundry. Outdoor amenities are designed for both relaxation and entertaining, featuring a beautifully integrated pool, an independent spa, expansive terraces and patios and a built-in outdoor grill. The flat, beautifully manicured grounds are complemented by an elegant courtyard with eight garage bays providing generous space for prized automobiles and collections alike. Combining timeless-inspired grandeur with modern luxury, this remarkable estate presents a rare opportunity to enjoy a private country-club lifestyle just minutes from downtown Armonk and Greenwich, with convenient access to New York City. A truly exceptional opportunity for the most discerning buyer.

Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom-built stone manor is a rare offering of timeless architecture, exceptional craftsmanship, and resort-like amenities. Encompassing more than 11,373 square feet and set upon 3.2 exquisitely landscaped level acres, the estate is surrounded by sweeping lawns, mature specimen plantings, and beautifully curated gardens that create an atmosphere of complete serenity and privacy. Designed for both grand-scale entertaining and comfortable family living, the residence features six bedrooms, eight bathrooms, and elegant interiors defined by high ceilings, abundant natural light, and refined architectural detailing. The main level boasts impressive 11-foot ceilings, gracious formal and informal rooms, a gourmet kitchen and oversized windows framing picturesque views of the grounds, pool, pool house and cottage with kitchen. The second floor, with 10-foot ceilings, is highlighted by an extraordinary primary suite offering a private sitting room, dual spa-inspired bathrooms, and two generous walk-in dressing rooms and a home office. Four additional en-suite bedrooms and a spacious laundry room complete this level. The thoughtfully designed lower level provides exceptional recreational and lifestyle spaces, including a guest bedroom and bathroom, family room, media room, fitness center, powder room, and additional space perfectly suited for the creation of a world-class wine cellar. The estate's outdoor amenities rival those of a private resort. A charming stone pool house with soaring ceilings, a fireplace, inviting living and dining areas, a kitchenette, changing room, and a full bathroom overlooks the spectacular 30' x 60' swimming pool and spa. Completing the compound is a beautifully appointed 1,500-square-foot guest house with two bedrooms, one full and one half bathroom, living room with fireplace, dining area, kitchen, office and an attached two-car garage, providing luxurious accommodations for extended family and guests. Offering an unparalleled combination of privacy, scale, and sophistication in one of Greenwich's most coveted locations, this exceptional estate represents the very best of country estate living just moments from town, schools, and commuter access.

Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate offers over 7,000 square feet of beautifully updated living space. Thoughtfully transformed, the home seamlessly blends the architectural character and craftsmanship of a bygone era with sleek contemporary design and today's most sought-after amenities. Elegant formal rooms, inviting gathering spaces, and 6 spacious bedrooms are complemented by 7 full baths, while 4 fireplaces add warmth and character throughout. The stunning grounds provide a true retreat, featuring a sparkling pool, expansive lawns, and exceptional privacy. A rare opportunity to enjoy historic charm and modern luxury!

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen--all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private oasis awaits--an expansive deck overlooking the river, scenic landscaping, and a stone patio with gunite pool--perfect for summer relaxation or entertaining under the stars. In addition to the numerous recent improvements to the key systems of the home, the driveway has been redone and the house has been painted on the interior and exterior. Whether you're looking for a peaceful retreat or a forever home, this extraordinary property offers an unparalleled lifestyle in an idyllic setting.

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot apartment with full kitchen and laundry. Leafy views from every room overlook the enchanting landscape. There is a pool with spa, fenced vegetable garden and fenced chicken coop. With so many aspects of special distinction, this is a wonderfully unique compound that captures the feel of the English countryside in a tranquil mid-country location. Includes legally permitted medical office.

Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with pristine white cabinetry and expansive granite surfaces-flows effortlessly into a fireside living room and adjacent sunroom with French doors leading outside. The outdoor experience is truly peerless, featuring a resort-style saltwater pool with waterfall, a professional-grade basketball/sports court, and a sprawling bluestone patio framed by artisanal rock walls and secure perimeter fencing. With a high-efficiency infrastructure, vast expansion potential in the walk-out basement, and a commute to Manhattan in under an hour, this property represents a rare opportunity to enjoy "like-new" luxury and a private backyard oasis without the wait.

A backyard worthy of a luxury resort, thoughtfully renovated interiors, and one of Westover's most desirable addresses...this is the home buyers have been waiting for. This exceptional five-bedroom home blends timeless architecture with sophisticated modern updates and an extraordinary backyard designed for everyday living and unforgettable entertaining. Minutes from downtown, Metro North and highways, you'll enjoy the rare combination of neighborhood charm, walkable streets, and generous property. Thoughtfully renovated from top to bottom, the floor plan offers effortless flow and abundant natural light. Easy entertaining in elegant living and dining rooms, home office, and a stunning chef's kitchen that serves as the heart of the home. Designed for both everyday living and entertaining, the kitchen features an oversized island, stainless steel appliances, quartz counters, and abundant cabinetry. Upstairs, the spacious primary suite offers a peaceful retreat with two walk-in closets and a luxurious spa-inspired bath. Four additional bedrooms and two full baths provide flexibility for family, guests, or work-from-home needs. The backyard is truly exceptional, with a heated saltwater pool and spa, complemented by an expansive deck, professionally designed landscaping, putting green, vegetable garden, and expansive lawn for recreation-- all fully fenced--offering beauty and privacy. This is a rare opportunity to enjoy luxury, comfort, and a luxury lifestyle.

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings, imported natural materials, and superb craftsmanship throughout, while a modern floor plan is designed for both entertaining and daily living. Stone terraces on every level overlook sweeping level lawns. Complete with a separate apartment for guests or staff, 7 garage bays, pool, and bocce court, this is unlike anything else on the market.

Historically known as ''Electric Hill,'' this extraordinary estate occupies one of the highest points in Mid-Country Greenwich, commanding year-round views of Long Island Sound across the treetops. Once part of a larger estate owned by Edward H. Johnson, Thomas Edison's associate and a pioneer in residential electrification, the property pairs a storied legacy with timeless architecture. Designed by renowned architect Mark Finlay and custom built by Hobbs, this stone Georgian stands as a testament to exceptional quality and enduring design. Set on more than five acres less than two miles from downtown Greenwich, the 12,000-square-foot residence offers rare privacy in one of Greenwich's most coveted locations. Crafted with meticulous attention to detail, the home features a hand-laid stone exterior, slate roof, limestone detailing, antique wood floors, custom millwork, and soaring ceilings throughout. Grand yet inviting, the interiors are defined by abundant natural light and beautifully proportioned living spaces, all thoughtfully oriented to maximize the home's southern exposure and sweeping views of Long Island Sound. The expansive chef's kitchen is designed for both everyday living and effortless entertaining, with a breakfast area overlooking the property. The dramatic family room showcases reclaimed wood beams spanning the cathedral ceiling, while a walnut-paneled, coffered library conceals a secret bookcase leading to a private home office known as the "Oval Office." Five generously sized en-suite bedrooms include a gracious first-floor guest suite and an elegant primary suite featuring dual walk-in dressing rooms and a private balcony offering the home's most spectacular view. The walk-out lower level is designed for recreation and entertaining, featuring a billiards room, media lounge, striking double-sided bar, home gym, and a climate-controlled 2,800-bottle wine cellar. Designed to embrace its remarkable setting, expansive bluestone terraces overlook formal gardens, sweeping lawns, and mature specimen trees, including a centuries-old beech tree. A gunite swimming pool and separate spa are complemented by a stone pool house crowned by a distinctive bell-cast pavilion roof, complete with a kitchenette and powder room. Together, these outdoor living spaces provide an ideal setting for indoor-outdoor entertaining with Long Island Sound as the backdrop. Few properties combine such extraordinary views, architectural pedigree, exceptional craftsmanship, and privacy just minutes from downtown Greenwich. Electric Hill represents one of Greenwich's most significant and irreplaceable estate offerings.

GREAT INVESTMENT OPPORTUNITY- Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly sophisticated modern lifestyle.The residence is distinguished by its extensive integration of advanced technology systems, seamlessly embedded throughout the home. Smart-home infrastructure (lighting, climate, security,and entertainment).State-of-the-art environmental and wellness technologies (air, water, energy efficiency,and comfort). Attached 2 car garage + 5 car carriage house w lifts. 45'x20' pool Features: Full house generator. Venetian plaster walls, bleached white oak and porcelain floors throughout, radiant heated floors (including garage), self cleaning glass beaded stucco exterior with composite slate roof, imported windows/doors and stone, and expansive property for sports and entertaining. Pet grooming room with separate laundry. Chef's kitchen and additional family kitchen. Separate staff quarters. Plans available for an additional indoor pool and underground parking garage for 8 more vehicles with a car elevator.